Rusty Jackhole 

When you have just the tip of your dick in a asshole, and you proceed to stroke your shaft until you unload your load of baby batter.

“She wouldn’t let me go deep. All I could get was a rusty jackhole”

Rusty Jackhole by Alex the cock Cannon April 12, 2019

Toxic Jackhole 

A narcisistic ex or current boyfriend who strings you along and keeps you hopelessly in love with him by telling you everything you want to hear, including, but not limited to, "you are my soul mate", "I've never had a connection with anyone like this in my life", etc. in attempt to fill his black hole of a soul. He is of course incapable of loving anyone but himself.

I changed Aaron's contact information in my phone to read Toxic Jackhole to prevent me from receiving his texts or phone calls.

Toxic Jackhole by I'm Done 888 April 24, 2011

jackhole 

To clarify, it was Jimmy Kimmel and Adam Carolla who invented the word while they were working on the Kevin & Bean morning show on KROQ.
Ah, those were the days.

Doc, the news guy, is a complete and utter jackhole!!

jackhole by Walking E July 13, 2006

Jackolicious 

The state of a drink when it has been "improved" by the addition of any whiskey product.

The game totally sucked until I got my jackolicious on.

Jackolicious by d^_^b February 27, 2008

Jackoodie

Jacket like apparatus, yet thin enough to wear as a hoodie. Usually fleece or fur lined with waterproof qualities.

Dude, nice Jackoodie!! Thanks, I got it for Christmas!!

It's too warm for a jacket, but I might get cold later......I'll bring my Jackoodie!!

Jackoodie by Toph Topherson December 23, 2010

Jackhole 

it is a combination of Jackass and Asshole and I started using the word back in 1985 at Perry High School

you are a jackhole if you think Jimmy Kimmel and Adam Carolla started this

Jackhole by Byron Woody May 30, 2018

Jackhole 

Someone who is an irritating, annoying, stuck up ding-dong. Not as bad as a**hole however is equivalent to a**hat.

Martha: OH MY GOD he is such a jackhole
Abby: Oh ya that's David

Jackhole by TheCultoftheBeatsproutGrowers October 23, 2019